25 Simpson Ave, Oak Bluffs, MA 02568

The advertised rate of $10,262/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 17, 2026.

Rates vary depending... on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be higher if billed in multiple payments.
Feel at home in this charming 3-bedroom home nestled in the heart of Oak Bluffs, offering the ultimate convenience and comfort. Located just above Sunset Park, this home is the ideal base for your island adventure and requires climbing a small set of stairs to enter.
This beautifully updated home offers a bright, open-concept living space and modern comforts. The fully equipped kitchen includes a gas stove, microwave, dishwasher, and all essential cookware. For your convenience, there is a washer and dryer, central heating and cooling, fresh linens, and bathroom essentials. Enjoy the outdoor deck with a dining table and chairs, and a private enclosed outdoor shower.
Free parking is available on the premises.
Walk to Oak Bluffs’ iconic attractions, including Oak Bluffs Marina, Circuit Avenue, Inkwell Beach, East Chop Beach, the Campground, and Ocean Park. With easy access to State Beach and the surrounding towns, this home is perfectly situated. Step into the back garden, where you’ll find a peaceful deck, perfect for enjoying morning coffee or evening cocktails.
This property is not pet-friendly, and unauthorized bringing of pets will incur a penalty of $300, which will go towards a deep cleaning of the property. Check-in time is after 4PM, and early check-in requests are subject to availability with an early check-in fee of $50 starting at 1 PM. Check-out time is before 11AM, and any unauthorized late check-out will result in a charge of $50 for every 30 minutes. Smoking is not allowed inside the property or outdoor spaces, and there is a smoking fine of $300 if there is evidence of smoking inside the property. Please observe quiet hours after 10PM and be mindful of the neighbors, as this property is situated in a quiet neighborhood. If the police are summoned due to noise complaints, this warrants a possible eviction with no refund. An extra charge of $100 will apply for not cleaning after using the barbecue grill.
Only bedding is provided; towels are not provided; you must bring your own towels. [SI] Read More